(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → 1-Cyclopropyl-3-(2-fluoro-4-methylsulfanyl-phenylamino)-1-H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide
Reaction equation
[OH:1][CH2:2][CH2:3][O:4][NH:5][C:6]([C:8]1[N:16]([CH:17]2[CH2:19][CH2:18]2)[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][C:22]=1[F:29])=[O:7].C[C:31]1(C)O[C@@H](CON)C[O:32]1>>[OH:1][C@H:2]([CH2:31][OH:32])[CH2:3][O:4][NH:5][C:6]([C:8]1[N:16]([CH:17]2[CH2:19][CH2:18]2)[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][C:22]=1[F:29])=[O:7]Participants
Reactant 2
Product 1
Procedure
The title compound was prepared in an analogous fashion to 1-cyclopropyl-3-(2-fluoro-4-methylsulfanyl-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2-hydroxy-ethoxy)-amide, replacing O-(2-vinyloxy-ethyl)-hydroxylamine with O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine. 1H-NMR (500 MHz, DMSO-d6). δ ppm 11.58 (broad s, 1H), 8.51 (d, J=0.83 Hz, 1H), 8.31 (d, J=5.87 Hz, 1H), 7.56 (dd, J=5.88, 1.20 Hz, 1H), 7.36 (s, 1H), 7.18 (dd, J=12.13, 2.50 Hz, 1H), 6.87 (dd, J=8.46, 2.50 Hz, 1H), 6.45 (t, J=8.99 Hz, 1H), 4.94-4.78 (m, 1H), 4.62-4.53 (m, 1H), 3.94 (dd, J=9.91 Hz, 1H), 3.76 (dd, J=9.85, 7.0 Hz, 1H), 3.73-3.66 (m, 1H), 3.56-3.47 (m, 1H), 3.42-3.31 (m, 2H), 2.41 (s, 3H), 1.15-1.08 (m, 2H), 0.87-0.83 (m, 2H); LC-MS (method C): [M+H]+=447.2, RT=0.479 min.
Sources & evidence
- ORD record
- ord-d6729a04ae5d4f498c8823b2f1ebc9ec
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855216B2
Reaction notes
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